Building With Squarespace

With CEO and Squarespace Expert, Kelsey Gilbert-Kreiling

How did you get started in web design? What are a few career highlights?

I got started using web design as a tool to communicate—when I was younger, of course I dabbled in making aesthetic modifications to my blog. But when I went to design school for fashion, I found myself drawn to using websites to collect and curate inspiration, and eventually started an online fashion publication. After years of using the web in that way, I found myself working in technology and editorial for a hospitality group in Chicago. They asked if I could build websites for new restaurants they were opening, and that really marked the transition from using the web as a tool to building websites as a service for others. 

The best part of design, as a medium, is the ability to spend your life creating art that solves problems. Over the years, we’ve collaborated with some incredible individual clients like Lucy Liu, Jessica Knoll, and Jenny Han. I will always be super proud of the work we do for non-profit organizations like YWCA and the Kennedy Center for Turnaround Arts. That said, I’m the most proud of the team we’ve built at Week of the Website—our designers, PMs, and agency team members are truly the best.  

What originally sparked your interest in Squarespace? How has your relationship with the platform grown over the years?

Squarespace really came along as the right tool for the job when I was working in hospitality—as an industry it has its own set of constraints (technical, financial, and time based) while also having pretty high expectations around design. How do you serve people very clear information while also creating a sense of place to invite them in? Squarespace came along at exactly the right time to give my clients beautiful websites they could use, edit, and own on a daily basis. 

The relationship has changed and grown so much. We’ve been very lucky to form a connection with the Squarespace team through enterprise projects and Squarespace Circle collaborations to help educate other designers. They feel like a partner in every way, which I recognize is so special.

We’ve always said that Squarespace sits at this perfect intersection of client usability and design team customization. And I love having the opportunity to reveal to folks what Squarespace can do.

What’s a common misconception marketers or clients have about Squarespace?

The biggest misconception is that it’s all a template. We basically never use prebuilt templates for our clients because frankly it’s so easy to begin from scratch. We’ve always said that Squarespace sits at this perfect intersection of client usability and design team customization. And I love having the opportunity to reveal to folks what Squarespace can do. braserochicago.com is a great example of how we can use the medium to create dynamic moments that don’t feel cookie cutter.

What made you decide to write Squarespace from Signup to Launch? How has the response been inside and outside the Squarespace community?

I was lucky enough to be contacted by the publisher, Packt, to gauge my interest in writing the book. I really enjoy the part of my job that lets me train and support other creatives through our agency,. So this was an interesting opportunity to expand on that. I used the book as a way not just to teach people about Squarespace, but to help them think like a web designer. And part of that was getting insight from lots of other leaders in the Squarespace design ecosystem. The response has truly been lovely. I’ve been on sales calls with people who have held up a copy, and it’s always amazing!

How do you see Squarespace, Wix, and similar web building platforms evolving over the next five years?

I really see AI not as an existential threat to web design but an expansion of the DIY mindset around building things on the internet. Site builder tools have always empowered individuals and small businesses to own their web presence. And I think, if these platforms can leverage generative technology in a really intelligent way, they stand to grow in interesting ways. I’m excited to see what happens next!

Can you tell us about the development of your week-long sprint process? What inspired it, and how has it matured?

When we began our business, my former partner and I were also doing large scale event production for galas, food festivals, and conferences. We got really, really good at project management. When we took a moment to step back and think about how we could approach our design practice differently, we realized that our ability to develop systems and processes that organized people could be hugely helpful in [terms of web development]. It was actually inspired by a meeting with the Squarespace team in 2015 while we were in NY for a different client job. Over the years, it’s become more sharply honed, but it uses many of the same foundations as it did then. 

How has the sprint impacted the culture of Week of the Website?

Because we work quickly, we have to hire people who are incredible listeners, empathetic collaborators, and curious people. We have a really close-knit culture for a fully remote team, and I think part of that is because, when you need to work quickly, you have to be comfortable asking for help or a new perspective. Just before this interview, one of my teammates was asking for thoughts on a technical feature for one of their projects, and I was able to share some resources that might get her unstuck. In a world that really prizes rugged individualism, our sprint model requires heartfelt collaboration. And over the years, we’ve realized just how special that is to find in creative team members.

What are some specific things you do to foster collaboration between individuals working in your agency?

Slack is huge! We have a very active company Slack that touches on technical questions, day-to-day project management, and the personal and fun. We do quarterly town hall meetings with breakout rooms for developers and PMs. These let us share in our community successes, update folks on goals or directional shifts, and build community. We also provide weekly updates of what’s going on in our community—who is launching a project, what we’re accomplishing as a team. That regular cadence of communication is important, and it helps us stay connected.

I’m always surprised how quickly the wins that would have seemed impossible at the beginning of your journey feel like everyday occurrences years in.

How has running an agency differed from what you initially thought it would be like? What did you find most surprising about the journey?

Oh, I had no idea what to expect when this all began over a decade ago. When I started this, I was 26 and basically everything about my life was different. Perhaps that’s the biggest thing: You and your business grow up together. It’s a longer road than the Make Money Online folks would have you expect. And I think I would have struggled less in the early years if I could have internalized that.  

I’m always surprised how quickly the wins that would have seemed impossible at the beginning of your journey feel like everyday occurrences years in. We joke that the hedonic treadmill is set on high in the agency life. So it’s a real practice to be able to step back and say, “this is what we once dreamed of.”

What advice do you have for anyone trying to balance being a mom and CEO?

I’ve found the most satisfaction in owning that this is how my life works. I’ve never tried to hide my work and the fact that I work hard from my child, and I think it’s good for him to see his mom be a leader and a creative thinker. I do, however, believe really strongly that you have to be present for either. When I’m parenting, I’m pretty conscious of not being on my phone trying to do work things. When I’m working, I try to give my full attention to work. Other people probably blend a bit better, but for me it feels like trying to do both at the same time ends with a lackluster outcome for either.

I’m about to have my second child. And, this time around, I’ve been ruthlessly proactive about planning to actually take time away to rest and recover before coming back. Last time I took a very short time away, and I think it prolonged my ability to be fully present for longer. This time, our team is so ready to carry on the torch, but we’ve also worked towards this for…about 9 months! Ultimately, I think it’s made our team stronger, and forced us to think about how we collaborate, delegate, and share responsibility among ourselves.

Share this on:

• LinkedIn
• X
• Threads
• Reddit
• Mail

About Kelsey Gilbert-Kreiling